Coordination Chemistry of Organoruthenium Compounds with Benzoylthiourea Ligands and their Biological Properties

Abstract

Benzoylthiourea derivatives feature several donor atoms capable of coordinating to metal centers. We report here a series of Ru(η6‐p‐cymene) complexes employing benzoylthiourea derivatives as ligands. Such ligands often coordinate to metal centers through their S and O donor atoms. We isolated complexes where the ligands were mono‐ or bidentately coordinated to Ru involving the S donor atom and surprisingly in bidentate coordination mode a deprotonated thiourea nitrogen resulting in a 4‐membered ring structure around the metal center. DFT calculations were used to explain the differences in coordination behavior. These were complemented by stability studies and biological investigations of the compounds as anticancer agents. Several of the synthesized derivatives exhibited significant cell growth inhibitory activity, with the complexes featuring bidentate ligands being more potent than their monodentate counterparts. This can be explained by the higher stability of the former under the conditions employed in cell culture assays.

Novel adamantyl clubbed iminothiazolidinones as promising elastase inhibitors: design, synthesis, molecular docking, ADMET and DFT studies

“…19–21 and in agriculture as an insecticide and weed killer. In addition, they are the precursor for the synthesis of a number of heterocyclic compounds and metal complexes 22 Acyl thiourea have also been applied as ion sensors and for the estimation of metal ions. 23–25 These electron-rich molecules act as ligand and organocatalysts in various asymmetric synthesis 26–28…”

“…[19][20][21] and in agriculture as an insecticide and weed killer. In addition, they are the precursor for the synthesis of a number of heterocyclic compounds and metal complexes 22 Acyl thiourea have also been applied as ion sensors and for the estimation of metal ions. [23][24][25] These electron-rich molecules act as ligand and organocatalysts in various asymmetric synthesis [26][27][28] Heterocyclic skeletons containing ve-member rings with two heteroatoms are promising core structures, commonly encountered in organic and medicinal chemistry.…”

Coordination Behavior of Acylthiourea Ligands in Their Ru(II)–Benzene Complexes─Structures and Anticancer Activity

“…10 Hartinger and co-workers reported a pH-monitored synthesis of the Ru(II)−arene complexes incorporating various acylthiourea ligands, which yielded a mixture of coordinated products whose separation was unsuccessful. 11 Recently, Grguric-S ̌ipka and co-workers reported the change in coordination of the acylthiourea ligand from monodentate to bidentate during the process of crystallization. 12 Thus, although a rich diversity of coordination modes is available for the acylthiourea ligands in Ru(II)−arene systems, their coordination behavior is not yet fully understood.…”

First Row Transition Metal Complexes Derived from N, Nʹ-Substituted Thiourea: Synthesis, Geometrical Structures and Cyclic Voltammetry Probe: A Review

“…nc/4.0/ -http://creativecommons.org/licenses/by ( their exhibition valuable efficiency in different applications such as analytical [36][37][38], and biological fields as insecticidal, antifungal, antithyroid, antitubercular, antibacterial, antitumor, antiviral and herbicidal [39][40][41][42][43][44][45][46], as well as to use them as selective agents to extract several specific worth metals like copper, cobalt, nickel, silver, palladium and gold to form more stable metal chelates [47][48]. In coordination chemistry, studies over the past decade have interested with transition metal complexes of benzoyl thioureas and provided important information on their properties [49][50][51].This interesting is related with the structural form of benzoyl thioureas which have carbonyl and C=S functional groups leading them to act as privilege chelating agents because of their capability to surrounding through the coordinating group metal centers [52]. In addition, It has previously been investigated the thermal behavior of the metal complexes of thioureas [53][54][55].…”